


Be Pretty

by DickBaggins



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean, Crossdressing, Dirty Talk, Exhibitionism, Fear, Fear of Discovery, Feminization, Forced Drinking, M/M, Mildly Dubious Consent, Public Sex, Rimming, Top Sam, Twink Dean, Voyeurism
Language: English
Status: Completed
Published: 2015-09-14
Updated: 2015-09-14
Packaged: 2018-04-20 17:22:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,739
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4795925
Author URL: https://archiveofourown.org/users/DickBaggins/pseuds/DickBaggins
Summary: <blockquote class="userstuff">
              <p>Dean dresses up to meet Sam at a bar and ends up with his skirt hiked up in an alley.</p>
            </blockquote>





	Be Pretty

Dean looked good. He knew he looked good, and he knew he _had_ to look good It was all for Sam. Been months since they'd seen each other, with Sam at college, and Dean was determined to pull out all the stops. And those stops were, specifically, a tiny pink skirt and a white crop-top, white knee socks and comfy pink Cons, and a fairly languid pose in a booth in the bar, in a quiet spot he'd scoped out earlier. He kept his eyes on the door, nervously swallowing and fiddling with the hem of his shirt, arranging and rearranging his skirt, legs crossed, uncrossed. He hoped Sam liked everything; the only instructions he had were a text with the address, time and 'Be pretty.'

Pretty  _was_ subjective, but the way Dean's eyes popped under the smokey makeup was not, that was gorgeous on every level. He already regretted getting here too early in case the makeup started to fail, in case someone else wanted to claim him first. But the opportunity to throw back the two quick shots made it kind of worth it, since he felt a bit calmer. Maybe not calmer but maybe...happier. More easy-going.

So that when Sam slipped up behind him and pressed against him with all that chest, Dean relaxed back into it right away like maybe he'd have done that to  _any_ big slab of meat that surprised him, but something instinctual must have known it was Sam. Or not. Whatever. It was warm and there was an arm slung over his shoulders, big tan hand brushing down his chest and squeezing at his pec just as Dean turned to look and actually confirm who it was.

He wanted to say something cocky and self-assured, some crack about Sam picking up strange, but as soon as his face was turned to Sam there was a shot glass against his lips, tilting up, and he opened his mouth and swallowed it without question. Sam's smirk jolted his dick, left him stunned for a moment. And just as he opened his mouth again to say his piece, Sam upended another shot into it and brushed his wide thumb over Dean's nipple, almost made him choke while it stiffened up under the thin white material.

“Nice tits,” Sam muttered, apparently exhausted of shots for the moment, thankfully. He tugged Dean out of his chair a little roughly, in a way that Dean didn't want to argue with. “Come.”

Dean tripped a little and went red, tucking under Sam's arm. He should ask where they were going, he shouldn't just blindly walk alongside his brother but he was fucking doing it anyway and it was just a dark corner of the bar, probably the darkest, furthest corner, where one table was shoved. Dean hadn't even noticed it when he scoped everything out. No one would notice.

When they were blanketed by shadows, Sam shoved Dean against the wall beside the only chair at the table, stroked his hands up his bare sides and kissed him hard, thoroughly, like owned him. Sam kissed him until he fucking melted into the wall, until he was boneless and even more pliant than before. Kissed him so long that when he pulled away, Dean gasped and sagged and groped out for his brother without even opening his eyes.

And then he did, and Sam was spread out on the chair, patting his lap, smirking again. “C'mere.”

Dean spun and sunk fast, perching precariously on one of Sam's thighs until he realized how big it was, how easy Sam was holding his weight, and he relaxed. His skirt was tented up and he tried to shove it down, palming at his dick at the same time, the whole no panties thing a really bad idea all of a sudden. He was still red, embarrassment prickling at him, mixing weird with the heat in his stomach that was definitely arousal.

Sam just watched him and when Dean was finished his flustered little attempt at modesty, Sam laid one hand on one of Dean's thighs and pushed his legs apart, so the skirt sprang up again. “You're easy.”

“I'm not,” Dean gasped, but his legs fell open wider when Sam slid his hand under the skirt, cupping at his balls, tracing the back of his hand up Dean's dick. He twitched against the smooth drag and by the time Sam made it up to his head, he was already leaking.

Sam hummed low in approval, his thumb slowly spreading around the mess in big, lazy circles. “ _Very_ easy. No bra, no panties, wet already. Pretty, like I wanted.”

Dean was relieved to hear that at least, biting at his lip and squirming in his brother's lap. He wanted to see if Sam was hard yet but he didn't want to ask, instead running his hand down Sam's chest, pawing playfully at his waistband. Sam let him do it, watching intently, still groping way too gently at Dean's dick.

“I could fuck you right here, probably,” Sam said thoughtfully, grasping at Dean's wrist, speeding his coy hand up so he was bumping his fingers against the hard ridge in Sam's jeans. “Would you like that?”

Dean gasped again, his eyes scanning around; he could see people, oh my god, they weren't walking towards him or looking or anything but he could see  _people_ and he shook his head, swallowing hard. “Can't, there's too many people.”

“I don't think they're looking at you, sweetheart.”

Dean tried to catch his breath, and reasonably, he knew Sam was right; no one had even been looking at Dean when he strutted in so either this was the dirtiest dive bar in the world, or they just genuinely did not care. Maybe both.

Sam's hand slid off Dean's dick and up to his chest, firmly groping at him again, easily finding his hard nipple and squeezing, rolling the material around it, making Dean's legs twitch.

“How 'bout the alley?” Sam suggested, breathing hot against his ear, just barely tilting his hips up against Dean's palm.

Dean could barely think, but alley, yeah, that sounded alright. He nodded hurriedly, whining out, “Yes, yeah, the alley.”

Sam laughed that low laugh Dean loved more than reasonable and gently gave Dean a shove until he stood up. He sat back a second, watching Dean try to right himself again, which as far as Dean was concerned, was an impossible task.

He was still red when he started walking out of the bar, restlessly shifting the skirt over his erection to no effect; it was there, it was unmistakable. He went quick, feeling the shadow of Sam behind him the whole time, just close enough that he was all heat and darkness. It made Dean's skin crawl with goosebumps, made his stomach wormy. Sam was fucking  _scary_ sometimes and it was the hottest fucking thing. What the fuck.

Dean avoided the puddles, not wanting to ruin his baby-pink Cons, tense with fear even though it was just  _Sam_ . He expected to be shoved face first into a wall, since that had happened before, but once they were halfway down the narrow alley, Sam's big hand latched onto Dean's shoulder and he spun him around, kissing him fierce, pushing him against the wall again.

The rough bricks against his back were altogether different than the smooth wood inside the bar. They bit hard through the thin material of his clothes, dug into where the crop top scooped down low and into his exposed back. Both of Sam's hands were at his chest, groping him and pushing him back harder against the rough stone, his fingertips digging in.

“Your fucking tits,” Sam growled against Dean's mouth.

“Already said that,” Dean panted.

“Did I call you a pretty girl yet?” Sam crooned, sliding a thigh between Dean's legs, forcing him to spread them while he tugged up his skirt again. “Cause you're a very pretty girl right now. Dripping for me. Cheeks all red. That the liquor? Or something else?”

It was _everything_ , Dean knew. It was the four quick shots and the heady embarrassment, the breakneck arousal and Sam's low, teasing voice. Dean didn't answer, figuring it was rhetorical dirty talk.

Sam bit at his jaw and shoved Dean's hand against his pants again, growling, “Well? What's got you blushing, pretty thing?”

Dean stuttered out some _noise_ , his mind a blank. Nothing in there but blurry hot arousal, wiped clean of basically everything from Sam and the whiskey. He just groped at Sam's dick through his jeans and arched up into his mouth, trailing down his neck now, biting at his collarbone and tugging his shirt down to get at his chest. The alley filled up with headlights and Dean gasped, shielding his eyes, squinting. Sam didn't move, latching his mouth around one of Dean's nipples, pulling at it with his teeth. Oh god, _someone was going to see, someone was probably already looking_ and Dean's free hand flew to Sam's hair, trying to tug him back.

“Sam – Sam, please?” He whined, “Someone's gonna see, gonna – fuck, Sam, _fuck._ ”

But Sam didn't move, just ground out a low laugh that Dean felt against his chest, and the headlights subsided quickly, leaving Dean's heart pounding so hard it hammered in his ears and made his vision red, throbbing around the edges.

“Scared, princess?” Sam asked with a distinct edge of amusement that kind of made Dean want to cry. “Little heart's pumping like a bird. Don't want anyone to see?”

“N-no,” Dean gasped, pressing against the weight of Sam's hips grinding into his, rucking the skirt up somewhere around his waist, rough denim against his bare dick, scraping, rubbing, so not enough.

“Then why are we in an alley?”

“That was your idea.”

“Coulda said no,” Sam hummed, finally raising his head from Dean's chest, his lips pinkish and puffy and smirking. “Not really in your vocabulary, I know. That's my favourite thing about you, I think.”

Dean wanted to protest but Sam was right. And even when he did say no to his brother, it was half-hearted, perfunctory at best.

“Well, second favourite,” Sam added, still smirking but all of a sudden sinking onto his knees, urging one of Dean's legs over his shoulder while he grabbed at his ass under the skirt. “My favourite's your bouncy little ass. Looks so good in your slutty skirt, Dean.”

Sam pressed Dean's dick up against his torso, quickly mouthing at his balls but he clearly had other things in mind. He roughly tilted Dean's hips against his mouth, supporting him one handed while his other prodded at Dean's ass, index finger ghosting over his hole and then something warmer, slick and searching and Dean reflexively pushed into it while his whole body flushed.

They were in an  _ alley _ and Sam was eating his ass and he was moaning for it like he always did, begging and grinding against his brother's tongue, louder and louder until it reverberated off the bricks, doubling back like the neediest goddamned chorus, twining with laughter swelling near the entrance. The sudden noise made Dean tense up and flinch away from Sam, but his brother's strong grip gave him nowhere to go.

“Sam, stop, someone's –  _ stop _ ,” Dean hissed, his eyes flickering at the alley' entrance, trying to peer into the darkness. 

Sam did  _ not _ stop. Dean felt him laugh against his ass and then there was a finger again, slicked up and pressing and Dean relaxed against it on instinct, even as the voices got louder, so, so nearby. Sam's first finger felt so fucking big, never ending and slow and he was still licking warm around Dean's rim, still squeezing at his dick with his other hand. Just squeezing, but when he pushed a second finger in too, and when the shadows danced across the alley, shuffled past on the street, it was enough. 

Dean nearly hiccuped his breath, shooting in a surprised twitch, throbbing under Sam's tight grip and splashing streaky jizz all over his skirt, over his exposed stomach. It was warm for a second, the fresh come and Dean's embarrassed, overheated body, but a cool breeze swept by and he shivered and nearly sobbed.

Sam didn't stop anything; he was still squeezing every little drop out of Dean's dick and fingering him, still pressing his tongue into his ass too, curling it alongside the crook of his fingers until Dean was shaking.

“Okay, okay,'” Dean panted, “Can we go? You – you did it, let's just go - “

Sam just laughed again, raising his head to blink up at Dean, his mouth curving into a puffy pink smirk. “No, remember what I said? You're gonna get fucked, Dean. Deserve it anyway, for how pretty you are, and how good you're being. Kind of. Little loud, though,” Sam added the last in a thoughtful way as he rose up off the concrete. 

But his fingers were still buried in Dean, pumping slick and faster until Dean was gritting his teeth, oversensitive and shaking.

“It's alright,” Sam hummed, leaning in and biting at Dean's exposed collarbone, kissing towards the hollow of his neck and sucking a welt up that made Dean's whole body arch against Sam's mouth. “I can just put my hand over your mouth when you get too loud. Cause, c'mon, you're gonna be loud with my dick up your tight little ass.”

“I can – I can be quiet,” Dean tried to assure him, but even he knew that was bullshit. Even anticipating it was making him whine louder than before, impossible to get a handle on.

“Don't want you to though,” Sam nuzzled at his neck, biting there too, licking at the sweat and sucking up mouthfuls of skin. “Want you loud, want everyone to hear you coming on my dick. Hear you begging. Everyone's gonna say, 'oh my god, what a slut,' and I'm gonna be fucking proud, Dean, that you're  _ my _ slut. My easy girl, dressed up so pretty, skirt all messed up. You're gonna mess it up again, y'know. Haven't even gone soft.”

Sam was right, Dean noticed, that even after spending, his dick was still hard and trapped between them, rubbing rough against his skirt and Sam and when he looked down and saw Sam slicking his own dick up with the standard emergency packet of lube, he moaned, eyes wide. Shit, Sam was going to fuck him in the alley. One single embarrassment wasn't enough.

“Ready?” Sam asked, low, his forehead resting against Dean, trapping out everything else through the curtain of hair.

Dean blinked, gritting his teeth, shaking his head. “No, Sam. C'mon,” he pleaded through a tight throat so everything came out high and desperate. And there was more he could do; he could try and shove at Sam, he could try and squirm away but his hands were balled fists at his sides instead.

“That  _ word _ ,” Sam snickered, “Sounds so good when you say it. Just makes me wanna do it more, y'know?” Sam twisted his fingers one last time inside Dean before he pulled out, grabbing Dean's ass in both hands and spreading, tilting him just right.

Dean could have fought that too, but the searching press, the cursory push of Sam's dick had him choking. Sam grunted and dragged in all the way, pushing all the breath out of Dean, shoving him against the wall and up onto his toes and Dean went fucking boneless. Pleasure seared through him and his arms draped heavy around Sam's neck so Sam had to hold him up, mashed against the wall and his solid chest while Sam swerved his hips slow and tried to rock deeper, even through there was nowhere else to go.

“Yeah, that's it,” Sam huffed, slinging one of Dean's legs around his waist, finally just starting to pull out a bit only to sink back in, “Good little back alley slutbag, Dean.”

All Dean could really manage was, “God,” and “fuck,” and “please,” although it wasn't clear, even to him, what he was begging for, more or less. Probably more. Sam's dick always felt like it was splitting him apart, especially at first, especially with no adjustment period. And especially at this angle, awkward and good and it shouldn't be so easy for Sam to manhandle him, to haul him around and fuck him against the wall but fuck all, it was happening and Dean couldn't stop it, especially after the four quick shots that were just fully hitting him, making his head spin off.

And he didn't want to stop it either, right then, for all the protestations that were still falling out of his mouth; every time he begged no, Sam just pounded harder, growled against him, bit his jaw, his neck, everywhere until Dean felt like one big nerve throbbing in time with his dick and Sam's thrusts. He sort of lost track of everything for a while, closed his eyes and gave into the sensations, gave into the noise spilling heedlessly from his lips that echoed in the alley, building a wall of sound that ignited even more heat in his body, pooling it in his stomach until he was just  _ that _ , just heat and pleasure while Sam fucked him. 

But, on a viciously hard thrust, something creaked beside Dean and he gasped surprised, turned his head and saw a dark green door swinging open and his heart thudded panic in his chest, his fingers scrabbling at his brother's back, unable to do anything but moan. 

Sam saw too though, raising his head from Dean's chest where he was busy marking him up, held himself fully inside Dean and shoved his hand against his mouth, hissing, “Quiet, bitch,” against his mouth just as someone came out.

Dean couldn't help it; he sobbed under Sam's hand and everything broke, the heat inside of him flaring, releasing, and he came between them with his eyes squeezed shut and Sam's hand hard against his mouth, his dick buried stock-still but throbbing inside of him while he tightened around it.

Oh god,  _ they were going to hear, going to hear him coming and see it, see him hauled up against the wall like a fucking whore, speared on his brother's cock. _

Their ragged breathing sounded so loud in Dean's ears and he was fucking terrified, opening his eyes again wide and rabbit-scared but the door was shutting just as quickly as it opened and Sam moved his hand off Dean's mouth so he could suck in desperately needed fresh air. But the only thing he got to do with it was push out a ragged moan because Sam started fucking him again, harder, fast and noisy, every thrust just slapping flesh and Dean's punched out noises and Sam growling while he sunk his teeth into Dean's chest where the crop top left him exposed.

They were way too loud,  _ so _ fucking clamorous and obvious and Dean couldn't even think to stop; everything was Sam's dick and the sticky mess between them and Sam's wolfish growling and his teeth and then he pushed up like a dagger into Dean, slamming him back against the wall while he came. And came, and came, throbbing like, forever while he sucked at Dean's chest, his fingertips digging into Dean's thigh. 

A parade could have marched through the alley for all Dean cared at that moment. They were sweaty stuck together and he was sticky messed up back and front and there was a delicious drag from Sam pulling out of him that made him moan again, breathy and useless, and he felt empty and somehow still needy, pressing against his brother.

“Fuck,” Sam swore sharply, his forehead sweaty against Dean's, kissing him hard and bruising, all teeth, “Fucking...prettiest alley slut, Dean, I swear.”

Dean whined again, twisting against Sam, shaking his head. “I'm not.”

“Yeah, you are,” Sam drawled, pushing Dean off so he thudded against the wall. Dean turned his head away, feeling Sam's eyes on him, making his face burn. Sam dragged his hand through the mess dripping down Dean's stomach, barely drying on his pink skirt and when Dean finally looked back, Sam was sucking it off his fingers.

Dean made a wholly mortifying noise, unable to stay still; he dove forward, sinking his mouth around Sam's jizz-sticky fingers, twirling their tongues together around the mess until it was clean. But his skirt was still stained and his stomach a little tacky, even as Sam tried to rearrange him. It looked awful, terribly...well, slutty was the only thing Dean's brain landed on.

“Alright,” Sam sighed out, righting his hair with one quick rake of his cleanest hand through it, grabbing Dean's arm and tugging him away from the wall. “More drinks?”

“No, Sam, I can't go anywhere like this.”

Sam just laughed and kept tugging, eventually tucking Dean under his arm and walking him right back in the bar. Dean was too embarrassed to even look up, his eyes firmly on his shoes, hazily noticing the smears of jizz even on the toes of his sneakers. Sam pushed Dean into the booth where he'd been before, holding up one finger and instructing him, “Wait.”

Dean frowned, huffed out a sigh, his ass still clenching while he shifted on the hard seat. He crossed his legs, flattening his skirt as best he could, wincing when Sam came back with a whole tray of shots, grabbing him again by the arm and dragging him into the dark back of the bar.

“To celebrate what a good little whore you are,” Same explained, sitting down heavily on the chair as before, legs spread, patting his lap, raising his eyebrows. “Sit.”

Dean stood in front of him, biting at his lip, tugging at his short top, eyeing the shots, eyeing Sam. And then he grinned, ducking his head and hopping on Sam's lap, winding his arms around Sam's neck and hiding in it. Sam obliged him for a minute or two, and then Dean felt the cold press of a shot glass against his cheek. He raised his head, blinking demurely at Sam and letting a smile ghost his lips while he brought it towards the glass and let Sam pour it in. 

When Sam said, “Good slut, so good,” he practically felt himself glowing, sitting up straighter, ruthlessly proud.

 

 


End file.
